NP-MRD: Showing NP-Card for Eriocalyxin K (NP0331537)

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Record Information

Version

1.0

Created at

2023-03-17 17:20:50 UTC

Updated at

2024-05-11 04:57:17 UTC

NP-MRD ID

NP0331537

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eriocalyxin K

Description

Speciociliatine belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group. It was first documented in 2022 (PMID: 36047661). Based on a literature review a significant number of articles have been published on Speciociliatine (PMID: 35854066) (PMID: 35472200) (PMID: 35468648) (PMID: 35335999).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032204042D          

 29 32  0  0  1  0            999 V2000
    0.6580   -3.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -2.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527   -2.6877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3053   -3.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290   -3.3303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -4.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053   -3.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763   -3.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236   -2.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8397   -1.9027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -2.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0387   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9995   -3.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662   -3.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2270   -4.2887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9210   -4.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -2.5934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0473   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -1.9509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7710   -1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9474   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5764   -2.0451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -2.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420   -0.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.1655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657   -0.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4183   -1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
  8 18  1  0  0  0  0
 11 18  1  0  0  0  0
 19  9  1  6  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
   -3.0373   -3.6251   -0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8564   -2.3344   -0.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1237   -1.3750   -1.0300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7911   -2.0155   -1.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316   -1.2369   -0.8784 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5147   -2.0573   -1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7110   -1.1202   -1.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5922   -0.2314    0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4378   -0.1530    0.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7021    0.7392    1.8799 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9445    1.2151    1.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6873    2.1261    2.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9825    2.4383    2.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5796    1.8344    1.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8308    0.9356    0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3995    0.3182   -0.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7134    0.5523   -1.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5338    0.6156    0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2492   -0.9729    0.5361 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0428   -0.2215    0.9082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8062   -0.0582   -0.3602 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8930    0.9034   -0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4023    1.3498    0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9789    0.9701    2.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8593    1.0428    3.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4480    1.4046   -1.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9552    0.9737   -2.7137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4673    2.3106   -1.7226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0014    2.7930   -2.9414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0670   -4.0106   -0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7933   -3.4969   -1.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3684   -4.4291   -0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2855   -2.5960    0.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8854   -1.9693    0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7355   -1.2016   -1.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880   -3.0287   -0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6559   -2.0991   -2.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6326   -2.7668   -0.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5024   -2.5705   -2.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6955   -0.5353   -1.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608   -1.6784   -1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380    1.0469    2.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2358    2.6003    3.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5819    3.1594    2.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6040    2.0668    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7113    1.5412   -1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4165    0.5755   -0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9522   -0.2464   -1.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2813   -1.9629    1.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7944    0.7828    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5272   -0.7923    1.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0225    0.3775   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2262    2.0794    0.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1794    2.0842    3.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4170    0.5943    4.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7725    0.4258    2.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9845    2.0464   -3.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0357    3.2022   -2.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4211    3.6797   -3.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
  9 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 22 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 21  3  1  0
 19  5  1  0
 18  8  1  0
 18 11  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  6
  4 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
 10 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 19 49  1  1
 20 50  1  0
 20 51  1  0
 21 52  1  6
 23 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 29 57  1  0
 29 58  1  0
 29 59  1  0
M  END


  Mrv1652309032204042D          

 29 32  0  0  1  0            999 V2000
    0.6580   -3.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -2.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527   -2.6877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3053   -3.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290   -3.3303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -4.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053   -3.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763   -3.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236   -2.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8397   -1.9027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -2.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0387   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9995   -3.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662   -3.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2270   -4.2887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9210   -4.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -2.5934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0473   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -1.9509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7710   -1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9474   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5764   -2.0451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -2.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420   -0.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.1655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657   -0.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4183   -1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
  8 18  1  0  0  0  0
 11 18  1  0  0  0  0
 19  9  1  6  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331537

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H]1CN2CCC3=C(NC4=CC=CC(OC)=C34)[C@H]2C[C@@H]1\C(=C/OC)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H30N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16+,19-/m1/s1

> <INCHI_KEY>
LELBFTMXCIIKKX-MYLQJJOTSA-N

> <FORMULA>
C23H30N2O4

> <MOLECULAR_WEIGHT>
398.503

> <EXACT_MASS>
398.220557454

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.354720147453634

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

> <ALOGPS_LOGP>
4.00

> <JCHEM_LOGP>
3.299593586666666

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.67027620485117

> <JCHEM_PKA_STRONGEST_BASIC>
7.042108351851677

> <JCHEM_POLAR_SURFACE_AREA>
63.79

> <JCHEM_REFRACTIVITY>
112.91320000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       1.228  -6.481   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.921  -5.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.458  -5.017   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.303  -6.305   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       5.841  -6.217   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.686  -7.504   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.223  -7.416   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.916  -6.041   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.071  -4.753   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       9.034  -3.552   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      10.475  -4.097   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.843  -3.391   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.139  -4.223   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.066  -5.762   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.697  -6.467   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.624  -8.006   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.919  -8.838   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.401  -5.635   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.533  -4.841   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.688  -3.554   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.151  -3.642   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.306  -2.354   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.768  -2.442   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.076  -3.818   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.462  -3.906   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.998  -0.979   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.153   0.309   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.536  -0.891   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.381  -2.178   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15    8   11                                                  
CONECT   19    9    5   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    3   22                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   22   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₈

Average Mass

422.4740 Da

Monoisotopic Mass

422.19407 Da

IUPAC Name

methyl (2E)-2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

Traditional Name

methyl (2E)-2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@]3(C(=O)[C@H]1C)C(=O)OC[C@@]14CC[C@H](OC(C)=O)[C@@](C)(CO)[C@@]1([H])C(O)O[C@H](C2)[C@]34[H]

InChI Identifier

InChI=1S/C22H30O8/c1-10-12-6-13-15-21(9-28-19(27)22(15,7-12)17(10)25)5-4-14(29-11(2)24)20(3,8-23)16(21)18(26)30-13/h10,12-16,18,23,26H,4-9H2,1-3H3/t10-,12+,13+,14-,15-,16+,18?,20+,21+,22-/m0/s1

InChI Key

PYFIJXXKLSSPNC-NVIRHUQUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 300.11, C5D5deposition_typeN, simulated)	Not Available	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
eriocalyx		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Corynanthean-type alkaloids

Sub Class

Not Available

Direct Parent

Corynanthean-type alkaloids

Alternative Parents

Substituents

Corynanthean skeleton
Beta-carboline
Pyridoindole
Quinolizine
3-alkylindole
Indole
Indole or derivatives
Anisole
Phenol ether
Alkyl aryl ether
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Pyrrole
Enoate ester
Methyl ester
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Amine
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4	ALOGPS
logP	3.3	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	16.67	ChemAxon
pKa (Strongest Basic)	7.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.79 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.91 m³·mol⁻¹	ChemAxon
Polarizability	45.35 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00025209

Chemspider ID

20124314

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Speciociliatine

METLIN ID

Not Available

PubChem Compound

15560576

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hughs M, Kish-Trier E, O'Brien A, McMillin GA: Analysis of Mitragynine and Speciociliatine in Umbilical Cord by LC-MS/MS for Detecting Prenatal Exposure to Kratom. J Anal Toxicol. 2022 Sep 1. pii: 6680066. doi: 10.1093/jat/bkac064. [PubMed:36047661 ]
Kamble SH, Berthold EC, Kanumuri SRR, King TI, Kuntz MA, Leon F, Mottinelli M, McMahon LR, McCurdy CR, Sharma A: Metabolism of Speciociliatine, an Overlooked Kratom Alkaloid for its Potential Pharmacological Effects. AAPS J. 2022 Jul 19;24(5):86. doi: 10.1208/s12248-022-00736-8. [PubMed:35854066 ]
Zhang M, Sharma A, Leon F, Avery B, Kjelgren R, McCurdy CR, Pearson BJ: Plant growth and phytoactive alkaloid synthesis in kratom [Mitragyna speciosa (Korth.)] in response to varying radiance. PLoS One. 2022 Apr 26;17(4):e0259326. doi: 10.1371/journal.pone.0259326. eCollection 2022. [PubMed:35472200 ]
Manwill PK, Flores-Bocanegra L, Khin M, Raja HA, Cech NB, Oberlies NH, Todd DA: Kratom (Mitragyna speciosa) Validation: Quantitative Analysis of Indole and Oxindole Alkaloids Reveals Chemotypes of Plants and Products. Planta Med. 2022 Apr 25. doi: 10.1055/a-1795-5876. [PubMed:35468648 ]
Tanna RS, Nguyen JT, Hadi DL, Manwill PK, Flores-Bocanegra L, Layton ME, White JR, Cech NB, Oberlies NH, Rettie AE, Thummel KE, Paine MF: Clinical Pharmacokinetic Assessment of Kratom (Mitragyna speciosa), a Botanical Product with Opioid-like Effects, in Healthy Adult Participants. Pharmaceutics. 2022 Mar 11;14(3). pii: pharmaceutics14030620. doi: 10.3390/pharmaceutics14030620. [PubMed:35335999 ]

Mu L, Li T, Wu PL, Cai LQ, Li SY, Wang ZY, Liu YY, Wang J, Yan D, Rao ZY, Wang CJ, Zhang J, Cao Y, Pan K, Yin ZQ: 5-epi-ent-Kaurane diterpenoids from the aerial parts of Isodon eriocalyx and their anti-atherosclerotic potential. Phytochemistry. 2023 May;209:113621. doi: 10.1016/j.phytochem.2023.113621. Epub 2023 Mar 7. [PubMed:36893826 ]

Showing NP-Card for Eriocalyxin K (NP0331537)

MOL for NP0331537 (Eriocalyxin K)

3D MOL for NP0331537 (Eriocalyxin K)

3D SDF for NP0331537 (Eriocalyxin K)

3D-SDF for NP0331537 (Eriocalyxin K)

PDB for NP0331537 (Eriocalyxin K)

3D PDB for NP0331537 (Eriocalyxin K)

SMILES for NP0331537 (Eriocalyxin K)

INCHI for NP0331537 (Eriocalyxin K)

Structure for NP0331537 (Eriocalyxin K)

3D Structure for NP0331537 (Eriocalyxin K)